Hydrochloric Acid → N-methyl-3-morpholino-2-(2-pyridyl)thiopropanamide

HRID 1111731Notes

Reaction equation

HRID 1111731 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1.C1([Li])C=CC=CC=1.[CH3:22][N:23]=[C:24]=[S:25].Cl>C1C=CC=CC=1.CCOCC.O.C1C=CC=CC=1>[CH3:22][NH:23][C:24](=[S:25])[CH:7]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)[CH2:8][N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11167Methyl isothiocyanateHCID 959094-(2-(2-Pyridyl)ethyl)morpholineHCID 178506676HCID 178506676, compound

Product 1

HCID 15581964N-methyl-3-morpholino-2-(2-pyridyl)thiopropanamide

Reagents, catalysts & solvents 3

HCID 241BenzeneSolvent2×HCID 962WaterSolventHCID 22174802Benzene etherSolvent

Procedure

N-[2-(2-pyridyl)ethyl]morpholine (12.7 g., 0.07 mole) in 60 ml. of dry benzene is added dropwise to 35 ml. of 2M phenyl lithium (0.07 mole) in benzene/ether with cooling. The mixture is stirred for 30 minutes, then methyl isothiocyanate (5.2 g., 0.07 mole), dissolved in 60 ml. of dry benzene, is added dropwise with cooling. The resulting solution is stirred overnight. An equal volume of water is added and the solution is cooled and made acidic with 10% hydrochloric acid. The phases are separated, the organic phase is washed with water, and the combined aqueous phases are made basic to about pH 9, then extracted with chloroform. The chloroform extracts are washed with water and dried over magnesium sulfate. Filtration and removal of solvent gives a residue which is recrystallized from ethyl acetate to give N-methyl-3-morpholino-2-(2-pyridyl)thiopropanamide.

Workup

  1. temperaturewith cooling
  2. stirringThe resulting solution is stirred overnight
  3. temperaturethe solution is cooled
  4. customThe phases are separated
  5. washthe organic phase is washed with water
  6. extractionextracted with chloroform
  7. washThe chloroform extracts are washed with water
  8. dry with materialdried over magnesium sulfate
  9. filtrationFiltration and removal of solvent
  10. customgives a residue which
  11. customis recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-bbfc17e6d5a8488c80a34cbd44f80e2f
Source dataset
uspto-grants-1978_10
Patent number
US04118567

Reaction notes

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